The goal of this project is the synthesis, characterization, and study of quinones derived from azulene, an important set of unknown compounds. Azuloquinones lie at the intersection of two broad avenues of research, viz. quinone chemistry and azulene chemistry, and should occupy a central position in the emerging family of nonbenzenoid quinones. These novel compounds command attention both as potential new antitumor agents and as organic compounds of theoretical interest. Although more quinones exhibit antitumor activity than do members of any other single class of compounds, nonbenzenoid quinones have never been examined for such activity. The structural features of many azuloquinones closely resemble the key features of known antitumor agents and thereby qualify these unusual compounds as promising candidates for biological testing. The azuloquinones will also provide a unique and serious test for current theories of structure, bonding and reactivity in organic molecules. The strengths and weaknesses of various theoretical methods (e.g., HMO, PMO, MINDO/3, ab initio STO-3G) have been well-established for calculations involving benzenoid and monocylcic nonbenzenoid pi-systems, but little is known in this regard with respect to fused pi-systems in which both rings are nonbenzenoid. The ideal study of this problem requires an extensive set of small, isomeric molecules, a role filled beautifully by the azuloquinones (eleven isomers, 18 atoms). Recent calculations predict that many of the azuloquinones will compare favorably to the known (isomeric) naphthoquinones in stability, reduction potential, etc. More than a dozen new derivatives of azulene hydroquinones have been prepared so far in this project. The biological activity of these compounds and methods for their oxidation to quinones are being explored.